Drake had barely arrived on stage Saturday at the packed First Midwest Bank Amphitheatre in Tinley Park and already he was wrestling with his contradictions.

“Lookin’ for the right way to do the wrong things,” he announced in “Lord Knows.” Drake, born Aubrey Drake Graham 25 years ago in Toronto, mixes swagger with regret, strip-club boasting with humble introspection. The sensitive hustler routine was massaged into a 90-minute show that affirmed his status as hip-hop’s new ladies man, hitmaker and powerbroker all rolled into one.

Drake leap-frogged from an acting career into hip-hop, and his wounded vulnerability and innocent swagger were soon championed by Lil Wayne. He capitalized on the hype with a series of song-stealing cameos on other artists’ singles, a well-received 2009 EP and mix tape, a million-selling 2010 debut album, “Thank Me Later,” and a 2 million-selling 2011 follow-up, “Take Care.”

On Saturday, he was a hip-hop king dressed in a drab T-shirt and baggy jeans. He’s playing venues 10 times the size of his first major tour two years ago, and the show has expanded accordingly. He was backed by a full band and a massive grid of 40 video screens that doubled as light portals. Despite the bigger production values and higher stakes, the show still had a loose feel, and the pacing sometimes lagged. It was marbled with cameos and a numbing 10-minute series of shout-outs to various audience members; the latter gambit was a charming detour on his first tour, but now it served only to bring a massive arena show to a grinding stand-still.

Yet Drake’s charisma as a performer and prowess as a hip-hop MC who’s not afraid to slip into some gray emotional areas was evident from the start. He channeled Southern gangsta rap on “Underground Kings” and then dealt with the consequences of an over-the-top lifestyle in “Over” (“I’m really too young to be feeling this old”). The sweetly yearning “Crew Love” professed devotion to family as greater than any personal accomplishment, while the gothic “Up All Night” indulged in puffed-up ego-tripping.

Drake opened up the stage to a series of protégés and friends, including 2 Chainz, Waka Flocka Flame and rising Chicago teen rapper Chief Keef who dutifully supplied the requisite stand-on-your-chair party rap. But once you’ve heard a song about ogling strippers, you probably don’t need to hear four.

Indeed, as Drake’s audience widens, the temptation to pander will intensify. Raps rhapsodizing about cash, hookers and hustlers will never go away, and Drake’s set had its share. “I guess it really is just me, myself and all my millions,” he crowed as “Headlines” filled the aisles with deliriously gyrating fans, vicariously sharing in the wealth.

But what makes Drake compelling is that he realizes the characters in his songs sometimes just sound like jerks. Guilt, remorse and vulnerability – he’s prone to all three. In “Amen,” performed with Meek Mill, Sunday morning gospel backslides into Saturday night decadence. The protagonists in Drake’s songs feel trapped between those two worlds, unable to fully commit to either.

Little wonder the most moving portions of this otherwise big, brassy concert were its most intimate. In “Take Care,” Drake responded to the recorded vocals of Rihanna, as if to underline the distance between a couple who can’t come clean about their true feelings for each other. The song concluded with a tumbling African rhythm, over which Drake danced, alone.

The repressed emotions spilled out in “Marvin’s Room,” in which the narrator drunk-dials his ex-girlfriend. Drake stood head bowed in a spotlight, mumbling and slurring his regrets into a microphone while thousands joined in.

The sing-along as pity party? Drake may not have invented that concept, but he sure owns it now.